Abstract
A mechanistic study of the thermal Garratt-Braverman/[1,5]-H shift of ene-diallene 6 leading to alkenes (E)-8 and (Z)-8 is reported. The product ratio was found to be temperature-independent and does not agree with the computed energy barriers (i.e., TS2E(⧧) and TS2Z(⧧)). On the basis of experimental and DFT computational results, we propose a mechanism that is strongly controlled by nonstatistical dynamic effects.
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